Fucose

From Wikipedia, the free encyclopedia
Jump to: navigation, search
L-Fucose
L-Fucose pyranose chemical structure.png
L-Fucose chemical structure.png
Names
IUPAC names
(3S,4R,5S,6S)-6-Methyltetrahydro-
2H-pyran-2,3,4,5-tetraol
Other names
6-Deoxy-L-galactose
Identifiers
2438-80-4 YesY
ChEBI CHEBI:2181 YesY
ChEMBL ChEMBL469449 YesY
ChemSpider 16190 YesY
Jmol-3D images Image
PubChem 17106
UNII 28RYY2IV3F YesY
Properties
C6H12O5
Molar mass 164.16
Supplementary data page
Refractive index (n),
Dielectric constantr), etc.
Thermodynamic
data
Phase behaviour
solid–liquid–gas
UV, IR, NMR, MS
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY verify (what isYesY/N?)
Infobox references

Fucose is a hexose deoxy sugar with the chemical formula C6H12O5. It is found on N-linked glycans on the mammalian, insect and plant cell surface, and is the fundamental sub-unit of the fucoidan polysaccharide. α(1→3) linked core fucose is a suspected carbohydrate antigen for IgE-mediated allergy.[1]

Two structural features distinguish fucose from other six-carbon sugars present in mammals: the lack of a hydroxyl group on the carbon at the 6-position (C-6) and the L-configuration. It is equivalent to 6-deoxy-L-galactose.

In the fucose-containing glycan structures, fucosylated glycans, fucose can exist as a terminal modification or serve as an attachment point for adding other sugars.[2] In human N-linked glycans, fucose is most commonly linked α-1,6 to the reducing terminal β-N-acetylglucosamine. However, fucose at the non-reducing termini linked α-1,2 to galactose forms the H antigen, the substructure of the A and B blood group antigens.

Anti-carcinogenic properties[edit]

The mushroom species Ganoderma lucidum AKA Reishi mushrooms contains alkaloid L-fucose, which has been found in polysaccharide and carbohydrate-based vaccine studies to have anti-tumor activity in mice with Lewis lung carcinoma cells. [3] Fucose is released from fucose-containing polymers by an enzyme called α-fucosidase.

L-Fucose is claimed to have application in cosmetics, pharmaceuticals, and dietary supplements.

See also[edit]

References[edit]